Outdoor Places - Vacation Rentals in Dudley Square

Harmony Medical Suites on Canal From US $210
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Oasis Guest House From US $130
         

9.4 (1402 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Great South End/Back Bay location, 1 bed condo near T station From US $414
         

10.0 (97 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Chic South End Studio With Patio From US $357
         

10.0 (103 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Modern townhome,Boston vacation,2 bath,pkg,deck From US $360
         

9.8 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly renovated pet friendly apt by parks and train! From US $189
         

8.0 (35 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Dudley Square

Over 3116+ Luxury Places to Stay in or Near Dudley Square

Top-Rated Vacation Rentals with a Pool in Dudley Square

Over 357+ Top-Rated Vacation Rentals with a Pool in or Near Dudley Square
South End Club Suites by Orchard From US $344
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxurious 3-bedroom apartment in vibrant Boston
New
From US $420
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hyatus Luxury Residences Boston South Bay Designer Collection From US $361
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Dudley Square

Over 1547+ Pet-Friendly Vacation Rentals in or Near Dudley Square
Boston vacation,Longwood Medical,mins to MBTA,pkg From US $163
         

7.8 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Bluebird Suites near MIT From US $143
         

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8.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Boston Harbor Hotel From US $530
         

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9.8 (1014 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Excellent 2 bedroom condo in South Boston From US $349
         

Right Near Convention Center and Train Station From US $483
         

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10.0 (28 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
14a-Cozy and well decorated apartment in awesome Boston From US $416
         

10.0 (27 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Heart of Southie - Hot Tub + Walk to Top Bars From US $809
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
14b-Charming, beautiful 3-bedroom apartment in Boston From US $416
         

10.0 (15 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Dudley Square

Over 273+ Large Vacation Homes & Villas in or Near Dudley Square
The Upton From US $129
         

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6.5 (13 Reviews)
Apartment
  • Air Conditioner
  • Breakfast
  • Internet
15 minutes to Historic Sights and World Cup Transport. From US $850
         

Spacious, New Renovation | Near T From US $800
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
Mid-Century Glam Retreat, Near T From US $415
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Spacious 5-Bedroom 3-full bath Boston Home, Subway access & Scenic View From US $458
         

Wheelchair Accessible Vacation Homes in Dudley Square

Over 1420+ Wheelchair Accessible Vacation Homes in or Near Dudley Square
Furnished Delx Studio w/Full Kitchen & Fast WiFi | Boston From US $311
         

Bluebird Suites in Kendall Square From US $169
         

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New
Apartment
  • Air Conditioner
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The College Club of Boston From US $194
         

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9.4 (1001 Reviews)
Bed & Breakfast
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety
Spacious 3BR in Heart of Downtown Boston! Family Favorite! From US $563
         

10.0 (58 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Bright & Spacious Loft Steps to the Freedom Trail From US $363
         

10.0 (52 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
King Bed Loft in the Heart of Downtown Boston From US $1,071
         

10.0 (37 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Back-Bay Upscale Central Condo Bos Common Downtown From US $463
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV

Dudley Square Varoom and Airbnb Places to Stay Under $200

Over 854+ Dudley Square Varoom and Airbnb Places to Stay Under $200
Newly furnished 1 bed, 1 bath. Views of the whole city! From US $153
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Chic Modern 2 bed Apartment with Exposed Brick From US $160
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Homestay In Fields Corner Area Boston From US $79
         

9.2 (7 Reviews)
Bed & Breakfast
  • Security/Safety
  • Restaurant
  • Guest Services
Quite 1 Bd Apt nearby MGH,MIT,Harvard W/D In Suite From US $182
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Sunny,spacious, sleeps 4, steps to MBTA,Hospitals. From US $160
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Renovated 2B, In-unit Laundry, Longwood, 1st Flr From US $179
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Sun-filled 1 bed, 1 bath in Brookline Village From US $163
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Dudley Square

Over 1884+ Instantly Bookable Vacation Homes in or Near Dudley Square
Entire Apt Downton Seaport (BEN-2010) From US $496
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Stunning South End/Back Bay Penthouse! From US $545
         

10.0 (97 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Beautiful Boston Brownstone! From US $540
         

10.0 (83 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
UltraLuxe Apt in Boston Brownstone in Prime Area From US $550
         

10.0 (76 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
🎖The Ashmont Suite - Close to Subway + Downtown🎖 From US $264
         

Hidden Gem 2 BR/1BA near Zoo 3 mil downtown Fenway From US $334
         

10.0 (20 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

About Dudley Square Vacation Rentals

With more than 3125 Dudley Square vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Outdoorplaces and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Dudley Square.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Outdoorplaces Dudley Square, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Dudley Square. Places to stay near Dudley Square are 557.62 ft² on average, with prices averaging $407 a night.

Outdoorplaces makes it easy and safe to find and compare vacation rentals in Dudley Square with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Dudley Square

Type Count
Holiday Apartments 2173
Vacation Homes 416
Hotels with Suites 373
B&B 12
Hostels 3
Others 1
Resorts 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Dudley Square

Pro Tip: Outdoorplaces makes it easy to compare the best listings on Outdoorplaces homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Outdoorplaces homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Dudley Square.

Weather in Dudley Square

View the weather forecast for Dudley Square before booking your Dudley Square Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F